Solid-State Structures and Properties of Lignin Hydrogenolysis Oil Compounds: Shedding a Unique Light on Lignin Valorization

This article explores the important, and yet often overlooked, solid-state structures of selected bioaromatic compounds commonly found in lignin hydrogenolysis oil, a renewable bio-oil that holds great promise to substitute fossil-based aromatic molecules in a wide range of chemical and material ind...

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Bibliographic Details
Published in:	International journal of molecular sciences Vol. 25; no. 19; p. 10810
Main Authors:	Driscoll, Oliver J, Van Hecke, Kristof, Vande Velde, Christophe M L, Blockhuys, Frank, Rubens, Maarten, Kuwaba, Tatsuhiro, van de Pas, Daniel J, Eevers, Walter, Vendamme, Richard, Feghali, Elias
Format:	Journal Article
Language:	English
Published:	Switzerland MDPI AG 01-10-2024 MDPI
Subjects:	Biorefineries Chemical properties Control Crystallography, X-Ray Epoxy resins Eugenol - chemistry glycidylation Guaiacol - analogs & derivatives Guaiacol - chemistry Hydrogen Bonding Hydrolysis Lignin Lignin - chemistry lignin epoxide lignin model Lignocellulose Materials Models, Molecular Molecular Structure Morphology Oils and fats Phenols Plant Oils Polyphenols Production processes single-crystal X-ray diffraction Structure Symmetry thermal properties X-Ray Diffraction Belgium glycidylation thermal properties CLP intermolecular energy calculations single-crystal X-ray diffraction crystal structure lignin model lignin lignin epoxide
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Summary:	This article explores the important, and yet often overlooked, solid-state structures of selected bioaromatic compounds commonly found in lignin hydrogenolysis oil, a renewable bio-oil that holds great promise to substitute fossil-based aromatic molecules in a wide range of chemical and material industrial applications. At first, single-crystal X-ray diffraction (SCXRD) was applied to the lignin model compounds, dihydroconiferyl alcohol, propyl guaiacol, and eugenol dimers, in order to elucidate the fundamental molecular interactions present in such small lignin-derived polyols. Then, considering the potential use of these lignin-derived molecules as building blocks for polymer applications, structural analysis was also performed for two chemically modified model compounds, i.e., the methylene-bridging propyl-guaiacol dimer and propyl guaiacol and eugenol glycidyl ethers, which can be used as precursors in phenolic and epoxy resins, respectively, thus providing additional information on how the molecular packing is altered following chemical modifications. In addition to the expected H-bonding interactions, other interactions such as π-π stacking and C-H∙∙∙π were observed. This resulted in unexpected trends in the tendencies towards the crystallization of lignin compounds. This was further explored with the aid of DSC analysis and CLP intermolecular energy calculations, where the relationship between the major interactions observed in all the SCXRD solid-state structures and their physico-chemical properties were evaluated alongside other non-crystallizable lignin model compounds. Beyond lignin model compounds, our findings could also provide important insights into the solid-state structure and the molecular organization of more complex lignin fragments, paving the way to the more efficient design of lignin-based materials with improved properties for industrial applications or improving downstream processing of lignin oils in biorefining processes, such as in enhancing the separation and isolation of specific bioaromatic compounds).
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1422-0067 1661-6596 1422-0067
DOI:	10.3390/ijms251910810